2,6-Dibromopyridine → 6-Bromopyridine-2-carbonitrile

HRID 228271Notes

Reaction equation

HRID 228271 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[C:9]([Cu])#[N:10]>CN(C=O)C>[Br:8][C:4]1[N:3]=[C:2]([C:9]#[N:10])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 122742,6-DibromopyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 151008596-Bromopyridine-2-carbonitrileYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Take up 2,6-dibromopyridine (0.500 g, 2.11 mmol) and CuCN (0.189 g, 2.11 mmol) in DMF (5.3 mL). Heat at 100° C. for 22 hours. Cool to room temperature. Add water (50 mL) and extract with ethyl acetate (3×100 mL). Wash the organic layer with brine (1×75 mL), dry over Na2SO4, filter and concentrate. Purify by flash chromatography, eluting with 15-40% ethyl acetate in hexanes to give the title compound (0.108 g, 30.0%): GC/MS, MS ES+ 182 (M−H)+, time 8.78 min, % of total 100%; TLC [silica gel 60 F254, 30% ethyl acetate in hexanes] Rf=0.29.

Workup

  1. temperatureCool to room temperature
  2. extractionAdd water (50 mL) and extract with ethyl acetate (3×100 mL)
  3. washWash the organic layer with brine (1×75 mL)
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by flash chromatography
  8. washeluting with 15-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-57f80f1c0c294069a6443a3ef19d55c7
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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